Tuscany Cycle

Tuscany Cycle Itinerary:

• Day 1

  Your trip begins today in Poggibonsi, Italy. Arrive in Italy and transfer on your own to the town of Poggibonsi, served by frequent bus and rail service from Florence. From Poggibonsi, a short taxi ride brings you to the lovely Hotel Villa Lecchi, a converted 18th-century Tuscan villa and our home for the next two nights. We’ll have some time to unpack and stroll around the picturesque grounds before meeting our guides for a welcome aperitivo followed by dinner at the hotel. Dinner and hotel included.

• Day 2

  After breakfast, we’ll gather in front of the hotel where our guides will give a safety talk and oversee the bike fitting before we begin our ride to Castellina in Chianti, one of Tuscany’s ancient fortified hilltowns whose origins date back to the 7th century B.C. The long, gradual uphill rewards us with stunning views over the idyllic Tuscan countryside. After lunch in Castellina, we cycle over rolling terrain dotted with farms, small villages and villas before a long descent brings us to Monteriggioni, whose stone wall and towers have guarded the approaches to Siena since 1338. We’ll return to the Villa Lecchi in late afternoon with time to relax or enjoy a dip in the pool before dinner. Cycling: 31 miles. Breakfast and dinner included.

• Day 3

  Our morning ride takes us along a quiet road that winds its way past olive groves and chestnut forests to a landscape dotted with villas and palaces built by wealthy Sienese between the 13th and 18th centuries. We stop for a mid-morning cappuccino in the village of Strove before continuing to a beautiful stand of chestnut trees; their overhanging boughs providing shade for our picnic lunch. The gothic towers of Siena materialize on the horizon as we continue our ride towards this enchanting city, ultimately pedaling right to the front door of our hotel, perfectly situated on the edge of Siena’s historic center. Late afternoon will afford the opportunity to shop, wander the medieval backstreets or just relax in the famous square (Il Campo) and watch local residents stroll by. Dinner is on our own tonight, although our guides will provide many dining recommendations from simple, yet delicious, pizza to numerous upscale and excellent restaurants. Cycling: 32 miles. Breakfast included.

• Day 4

  Siena, originally established as a Roman military colony in the first century B.C., is home to an incredible number of artistic and architectural treasures. This morning, we’ll take a guided tour of the city and learn about its unique history and culture including the significance of the world renowned Palio horse race and the important role it still plays in the life of local citizens. After lunch, we’ll change into our bike clothes and begin our afternoon ride. Those who have seen Bertulucci’s Stealing Beauty or The English Patient will immediately recognize the Crete Senese, with its vast undulating wheat fields punctuated by majestic cypress trees and the occasional farmhouse. We’ll spend much of the afternoon exploring this haunting region located in the central Tuscan countryside before arriving at our next hotel in Asciano. This charmingly authentic small town has a history of some 2,500 years and a fascinating museum that recounts the history of the Etruscan people (who gave their name to Tuscany). The Etruscans were Aegean settlers whose civilization flourished in Italy from the ninth through the first century B.C. when they where ultimately granted Roman citizenship and eventually absorbed by the growing empire. Enjoy a guided wine tasting at dinner this evening. Overnight in Asciano for the next two nights. Cycling: 28 miles. Breakfast and dinner included.

• Day 5

  We begin the day with a ride to the fabulous red brick monastery of Monte Oliveto Maggiore.  Bernando Tolomei, a successful and pious Sienese merchant, founded the Benedictine order of Monte Oliveto Maggiore in 1313 and the monastery became a hermitage for the regional elite.  Upon arrival, we’ll seek out the Great Cloister where the walls are decorated with 36 marvelous frescoes depicting the life of St. Benedict.  Later today, we’ll continue our ride through a string of delightful hilltop villages, stopping for lunch at a local osteria in the town of Montisi, before returning to Asciano and our familiar hotel.  Tonight is pizza night at the wonderful Pizzeria Ristorante La Mencia (a variety of other delicious homemade main courses will be available as well).  Cycling: 33 miles.  Breakfast and dinner included.

• Day 6

  A gorgeous ride to the striking hilltop town of Montepulciano takes us along small roads that wind their way up, around and between tiny villages surrounded by olive groves and vineyards. We’ll stop en route to visit a producer of giant terracotta urns and planters and learn about the crafting process from raw clay to finished product. Our hotel is located inside the walls of Montepulciano and affords spectacular views to the south over the Orcia Valley and out towards the Lago di Trasimeno. There is time to explore the town's labyrinth of narrow streets and enjoy a cool glass of Prosecco in the main piazza before dinner (on our own tonight). Cycling: 25 miles.  Breakfast included.

• Day 7

  Our Tuscan cycling adventure ends with a fantastic ride to Pienza and the pastoral Orcia Valley. All of Pienza’s major buildings were constructed between 1459 and 1462 as Pope Pius II, a local boy, issued a Papal Bulletin decreeing that Pienza was to be a regional center of art. The Duomo was one of the first Renaissance cathedrals in Tuscany and was consecrated in 1462.  This afternoon, our route drops down into the green and golden hills of the Orcia Valley and takes us to the charming village of Monticchiello for lunch before one final rolling ride brings us back to Montepulciano.  A special farewell dinner has been planned for this evening – a final opportunity to enjoy the region’s renowned cuisine and toast one another with the town's famous Vino Nobile di Montepulciano. Cycling: 30 miles or an optional 40 miles. Breakfast and dinner included.

• Day 8

  After breakfast, we transfer to the Chiusi train station for rail connections to Rome or Florence. From these gateway cities, we can catch our flights back to the U.S. or opt to extend our Italian holiday. For those flying out today, please do not schedule a flight prior to 3 p.m. Breakfast included.

Although we do our best to adhere to the schedule listed above, this itinerary is subject to change for numerous reasons beyond our control.

If you are traveling alone and specifically request single accommodations, you will be asked to pay the full single supplement noted on the trip itinerary. If you wish to share accommodations, we will assign you a roommate if one is available. If a roommate cannot be found, you will be asked to pay a reduced single fee, which is half of the full single supplement. Please be advised that there are a limited number of single rooms available on most departures.

All accommodations as noted; meals as noted in the daily itinerary; bilingual guides; support vehicle; sightseeing as noted; bicycles (27-speed hybrid style); wine tasting on Day 4.

Round-trip airfare; airport/hotel transfers; 2 dinners and 6 lunches; travel insurance; excess baggage charges; gratuities; alcoholic beverages and items of a personal nature. Please bring your own bike helmet, as you will be required to wear one.

This trip is rated as Moderate Plus [3-4] and consists of a combination of moderate and more vigorous cycling days covering 30-40 miles over predominantly hilly terrain. Although a support vehicle will be available, participants should be experienced cyclists who enjoy spending much of the day (4-6 hours) on their bikes. The countryside in Tuscany is rarely flat, so a regular conditioning program beginning at least three months prior to departure is strongly recommended. Cycling, walking/running and a daily stretching regimen are all great ways to prepare for this adventure.

We have scheduled our departures to avoid mid-summer heat and crowds while still traveling during periods that typically offer an ample amount of sunshine. Temperatures during our visits generally range from 70° to 80° F during the day, dropping 10-15 degrees at night (early spring and fall departures will have slightly cooler temperatures). Rain is possible on any of the departures, and while not typical, does necessitate that participants arrive equipped with appropriate raingear (see Gear List).

This trip is subject to the booking information set forth in the current REI Adventures Reservation Information. Please read this information carefully and call us if you have any questions. A full gear list and pre-departure information is sent upon sign-up. We highly recommend the purchase of travel insurance through REI Adventures. If coverage is purchased within 21 days of your initial trip deposit, the 'Pre-existing Conditions Exclusion' is waived (certain exclusions apply).

We look forward to having you join us for the trip of a lifetime! Why wait? Space is limited, reserve your adventure today.

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